Guided tour

From Siena: Chianti and Castles Tour with Wine Tastings

4.5 / 5

99 reviews

Activity provider: My Tour in Italy
Guided tour

From Siena: Chianti and Castles Tour with Wine Tastings

Activity provider: My Tour in Italy
Likely to sell out

From US$ 92.70 per person

Likely to sell out

Explore the scenic wine region of Chianti on a half-day tour from Siena. Enjoy a Tuscan landscape of gently rolling hills and vineyards and taste Chianti wines paired with Tuscan products.

About this activity

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Duration 5 hours
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Live tour guide
English, Spanish, Italian


  • Discover the breathtaking landscapes of Chianti via minivan
  • Explore ancient churches, medieval castles, and small villages
  • Visit 2 renowned wineries in the Chianti area
  • Savor bruschetta paired with typical Tuscan cold cuts and cheese
  • Visit the Castellina in Chianti
Full description

Immerse yourself in picturesque Tuscan scenery on a sightseeing day trip from Siena to the region of Chianti. Visit the Castellina in Chianti before partaking in a wine tasting experience at a wine estate.  

Board a spacious and climate controlled van in a centrally-located meeting point in Siena. Admire the Italian countryside on the ride as you pass thorugh pristine landscapes that have been cradling the Chianti vineyards for centuries.

Discover a harmony of colors that can only be found in the hills of this region. Delight your senses as you dive into the sounds, scents, and flavors of this land will capture your senses through this unique experience. 

Visit ancient churches, medieval castles, and small villages where the rhythm of life remains unaltered over time. Continues to a charming wine estate. 

Indulge in a wine tasting paired with typical Tuscan food. View the beautiful ruby-red color and the characteristic bouquet with scents of violet are the special to Chianti wine. Savor this blend of Sangiovese, Canaiolo, Merlot and Cabernet Sauvignon grapes.

Later, move on to another winery in the middle of the Chianti Classico area, where you’ll have a second optional wine tasting alongside an extra virgin olive oil tasting. The tour will end with a return to Siena.

  • Transportation via minivan
  • Bilingual guide
  • Multistop tour
  • Visit at 2 Chianti wineries, one of which is exclusive
  • Extra virgin olive oil tasting
  • 1 wine tasting
  • Tips (optional)
  • The second wine tasting
Not suitable for
  • Wheelchair users

Select participants and date



Meeting point

Meeting point may vary depending on the option booked.

Important information

Know before you go

  • You must be able to climb and descend stairs
  • This is a small-group tour with a maximum of 8 people in the minivan
  • You can request the pickup and drop-off service for an extra of 20€, within 10 km of the center of Siena. This service will be available starting from April 1, 2023
Customer reviews

Overall rating

4.5 /5

based on 99 reviews

Review summary

  • Guide
  • Transportation
  • Service
  • Organization

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We visited two wineries with tastings and a few small towns. The first winery gave us a plate of sliced meat and cheese. The driver guide did a very good job. We had a good time and bought some wine. The only problem was there was no step stool to get into the van. This is difficult for people like me so I needed help from someone every time.

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March 31, 2023

The tour was very nice, our tour guide was on time and explained some nice facts about the Chianti region and wines on the way. We visited beautiful privately owned Castello di Brolio and winery and then a winery in Lornano. It's a nice tour and we recommend it because it not long and starts in the afternoon at 2pm.

March 31, 2023

Experience was good , possibly the 1st stop for wine tasting may have been more interesting if we had have been told about the types of wine more it was a bit light on info . The drivers were great and the stops at the castle and village also the last stop was really good and I bought some wine also

March 31, 2023

Product ID: 8413